Why does Toby wear a wedding ring?
Richard Schiff decided of his own initiative that Toby should wear a wedding ring, as part of the back-story he imagined for the character (which probably involved him being a widower). This was completely unbeknownst to writer/executive producer Aaron Sorkin, who was very surprised halfway through the first season to realize that Toby had been sporting a wedding ring all along. At that point Sorkin had already decided to introduce Toby s ex-wife, so we re now left with the somewhat bizarre scenario of a man who s been divorced for quite some time but still wears his ring.